3-(4-Methyl­phen­yl)-1-(2-pyrrol­yl)prop-2-en-1-one

In the title compound, C₄H₁₃NO, the pyrrole and benzene rings are almost coplanar, with a dihedral angle of 2.90 (1)° between them. In the crystal structure, mol­ecules form centrosymmetric dimers through N—H...O hydrogen-bonding inter­actions. Neighbouring mol­ecular pairs are held together by face-to-face π–π stacking inter­actions between adjacent pyrrole rings [perpendicular inter­planar distance = 3.3948 (3) Å and centroid-to-centroid distance = 3.723 (2) Å], forming one-dimensional chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.051
• wR factor = 0.145
• Data-to-parameter ratio = 15.3

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S1. Comment

Chalcones have attracted considerable interest as a template in the development of biology. The anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000; Opletalova & Sedivy, 1999). The objective of this study therefore synthesize and elucidate the crystal structure of a new chalcone compound, (I), Fig. 1.

The pyrrole ring, benzene ring and the enone group of the molecule containing atoms O1, C5, C6 and C7, are almost co-planar with the maximum deviation 0.0702 Å for C7. The short H6···H9 (2.25 Å) contact causes the bond angles C7—C8—C9 [123.1 (2)°] C6—C7—C8 [127.7 (1)°] to deviate significantly from 120°.

In the crystal, molecules form inversion related dimers through N—H···O hydrogen bonds. Neighboring pairs are further linked by face-to-face π–π stacking interactions between adjacent pyrrole rings [perpendicular interplanar distance 3.3948 (3) Å and centroid-to-centroid distance 3.723 (2) Å], forming one-dimensional chains, Fig. 2.

Related literature

For details of the biological properties of chalcones, see: Dimmock et al. (1999); Go et al. (2005); Opletalova (2000); Opletalova & Sedivy (1999). For related structures, see: Kumaran et al. (1996); Shanmuga Sundara Raj et al., (1997, 1998).

S2. Experimental

2-Acetylpyrrole (4.36 g, 40.0 mmol) was added to a solution of p-tolualdehyde (2.42 g, 20.0 mmol) in methanol (130 ml). Potassium hydroxide (2.24 g, 40 mmol) and ammonia (25%, 100 ml) were then added to the solution and refluxed for 36 h. The yellow precipitate that formed was removed by vacuum filtration, washed with water to neutral pH. The product was recrystallized from chloroform/ethanol (3:1) to yield 2.10 g (49%) of the title compound.

S3. Refinement

All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and N—H = 0.86 Å, U_iso = 1.2U_eq(C or N) for aromatic, ethylene and nitrogen; 0.96 Å, U_iso = 1.5U_eq(C) for CH₃ atoms.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius.
	Fig. 2. Packing diagram showing the N—H····O hydrogen bonding and face-to-face π–π stacking interactions interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

3-(4-Methylphenyl)-1-(2-pyrrolyl)prop-2-en-1-one

Crystal data

C14H13NO	F(000) = 448
Mr = 211.25	Dx = 1.217 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1908 reflections
a = 8.6236 (11) Å	θ = 2.4–26.2°
b = 5.6273 (7) Å	µ = 0.08 mm^−1
c = 23.958 (3) Å	T = 295 K
β = 97.305 (2)°	Prism, yellow
V = 1153.2 (3) Å^3	0.43 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2241 independent reflections
Radiation source: fine-focus sealed tube	1757 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.892, Tmax = 0.985	k = −6→6
6514 measured reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0733P)^2 + 0.198P] where P = (Fo^2 + 2Fc^2)/3
2241 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.41397 (15)	0.4506 (2)	0.42156 (5)	0.0652 (4)
N1	0.65056 (16)	0.2223 (3)	0.49341 (6)	0.0550 (4)
H1	0.6209	0.3507	0.5084	0.066*
C1	0.10198 (19)	−0.0007 (3)	0.15386 (7)	0.0524 (4)
C2	0.2228 (2)	−0.1227 (3)	0.18472 (8)	0.0610 (5)
H2	0.2580	−0.2638	0.1705	0.073*
C3	0.2927 (2)	−0.0405 (3)	0.23608 (8)	0.0628 (5)
H3	0.3739	−0.1269	0.2558	0.075*
C4	0.24344 (18)	0.1698 (3)	0.25891 (7)	0.0500 (4)
C5	0.1241 (2)	0.2946 (3)	0.22729 (7)	0.0565 (5)
H5	0.0903	0.4378	0.2409	0.068*
C6	0.0545 (2)	0.2104 (3)	0.17596 (7)	0.0587 (5)
H6	−0.0257	0.2973	0.1559	0.070*
C7	0.0241 (2)	−0.0992 (4)	0.09886 (8)	0.0699 (6)
H7A	0.0887	−0.0688	0.0698	0.105*
H7B	−0.0757	−0.0241	0.0893	0.105*
H7C	0.0098	−0.2674	0.1024	0.105*
C8	0.30938 (19)	0.2592 (3)	0.31416 (7)	0.0532 (4)
H8	0.2768	0.4098	0.3237	0.064*
C9	0.40985 (19)	0.1515 (3)	0.35225 (7)	0.0566 (5)
H9	0.4450	0.0004	0.3443	0.068*
C10	0.46818 (18)	0.2609 (3)	0.40658 (7)	0.0521 (4)
C11	0.59111 (18)	0.1372 (3)	0.44173 (7)	0.0495 (4)
C12	0.6710 (2)	−0.0694 (3)	0.43344 (8)	0.0589 (5)
H12	0.6556	−0.1664	0.4018	0.071*
C13	0.7789 (2)	−0.1066 (4)	0.48098 (8)	0.0669 (5)
H13	0.8493	−0.2320	0.4869	0.080*
C14	0.7621 (2)	0.0753 (3)	0.51726 (8)	0.0627 (5)
H14	0.8186	0.0943	0.5527	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0716 (8)	0.0628 (8)	0.0578 (8)	0.0086 (6)	−0.0054 (6)	−0.0152 (6)
N1	0.0557 (8)	0.0583 (8)	0.0494 (8)	0.0015 (7)	0.0008 (6)	−0.0053 (7)
C1	0.0536 (9)	0.0589 (10)	0.0450 (9)	−0.0076 (8)	0.0074 (7)	−0.0022 (8)
C2	0.0626 (10)	0.0620 (11)	0.0579 (11)	0.0063 (9)	0.0055 (8)	−0.0173 (9)
C3	0.0562 (9)	0.0701 (12)	0.0590 (11)	0.0146 (9)	−0.0041 (8)	−0.0137 (9)
C4	0.0478 (8)	0.0540 (10)	0.0478 (9)	−0.0044 (7)	0.0048 (7)	−0.0057 (7)
C5	0.0698 (11)	0.0469 (9)	0.0520 (10)	0.0039 (8)	0.0050 (8)	−0.0030 (8)
C6	0.0656 (10)	0.0595 (10)	0.0483 (10)	0.0061 (8)	−0.0025 (8)	0.0035 (8)
C7	0.0754 (12)	0.0805 (14)	0.0513 (10)	−0.0049 (10)	−0.0013 (9)	−0.0107 (9)
C8	0.0524 (9)	0.0557 (10)	0.0517 (10)	−0.0034 (7)	0.0072 (8)	−0.0099 (8)
C9	0.0536 (9)	0.0600 (10)	0.0544 (10)	0.0008 (8)	−0.0001 (8)	−0.0125 (8)
C10	0.0473 (8)	0.0564 (10)	0.0523 (10)	−0.0052 (7)	0.0055 (7)	−0.0071 (8)
C11	0.0468 (8)	0.0562 (10)	0.0454 (9)	−0.0066 (7)	0.0044 (7)	−0.0045 (7)
C12	0.0599 (10)	0.0595 (11)	0.0576 (10)	−0.0013 (8)	0.0093 (8)	−0.0070 (9)
C13	0.0639 (11)	0.0679 (12)	0.0676 (12)	0.0120 (9)	0.0033 (9)	0.0052 (10)
C14	0.0601 (10)	0.0723 (12)	0.0531 (10)	0.0000 (9)	−0.0025 (8)	0.0044 (9)

Geometric parameters (Å, º)

O1—C10	1.237 (2)	C6—H6	0.9300
N1—C14	1.340 (2)	C7—H7A	0.9600
N1—C11	1.365 (2)	C7—H7B	0.9600
N1—H1	0.8600	C7—H7C	0.9600
C1—C2	1.382 (2)	C8—C9	1.323 (2)
C1—C6	1.384 (2)	C8—H8	0.9300
C1—C7	1.506 (2)	C9—C10	1.470 (2)
C2—C3	1.379 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.446 (2)
C3—C4	1.393 (2)	C11—C12	1.379 (2)
C3—H3	0.9300	C12—C13	1.392 (2)
C4—C5	1.389 (2)	C12—H12	0.9300
C4—C8	1.462 (2)	C13—C14	1.362 (3)
C5—C6	1.381 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C14—N1—C11	109.67 (15)	C1—C7—H7C	109.5
C14—N1—H1	125.2	H7A—C7—H7C	109.5
C11—N1—H1	125.2	H7B—C7—H7C	109.5
C2—C1—C6	117.49 (15)	C9—C8—C4	127.73 (17)
C2—C1—C7	120.48 (17)	C9—C8—H8	116.1
C6—C1—C7	122.02 (16)	C4—C8—H8	116.1
C3—C2—C1	121.66 (17)	C8—C9—C10	122.63 (17)
C3—C2—H2	119.2	C8—C9—H9	118.7
C1—C2—H2	119.2	C10—C9—H9	118.7
C2—C3—C4	121.01 (16)	O1—C10—C11	121.51 (15)
C2—C3—H3	119.5	O1—C10—C9	121.28 (15)
C4—C3—H3	119.5	C11—C10—C9	117.21 (15)
C5—C4—C3	117.21 (15)	N1—C11—C12	106.82 (14)
C5—C4—C8	119.73 (15)	N1—C11—C10	121.50 (15)
C3—C4—C8	123.05 (15)	C12—C11—C10	131.68 (15)
C6—C5—C4	121.33 (16)	C11—C12—C13	107.66 (16)
C6—C5—H5	119.3	C11—C12—H12	126.2
C4—C5—H5	119.3	C13—C12—H12	126.2
C5—C6—C1	121.27 (16)	C14—C13—C12	107.15 (17)
C5—C6—H6	119.4	C14—C13—H13	126.4
C1—C6—H6	119.4	C12—C13—H13	126.4
C1—C7—H7A	109.5	N1—C14—C13	108.70 (16)
C1—C7—H7B	109.5	N1—C14—H14	125.7
H7A—C7—H7B	109.5	C13—C14—H14	125.7
C6—C1—C2—C3	1.0 (3)	C8—C9—C10—O1	7.2 (3)
C7—C1—C2—C3	−177.82 (18)	C8—C9—C10—C11	−172.94 (16)
C1—C2—C3—C4	0.1 (3)	C14—N1—C11—C12	−0.66 (19)
C2—C3—C4—C5	−1.4 (3)	C14—N1—C11—C10	179.84 (15)
C2—C3—C4—C8	177.45 (18)	O1—C10—C11—N1	1.2 (3)
C3—C4—C5—C6	1.6 (3)	C9—C10—C11—N1	−178.62 (15)
C8—C4—C5—C6	−177.28 (16)	O1—C10—C11—C12	−178.12 (17)
C4—C5—C6—C1	−0.5 (3)	C9—C10—C11—C12	2.0 (3)
C2—C1—C6—C5	−0.8 (3)	N1—C11—C12—C13	0.1 (2)
C7—C1—C6—C5	178.01 (18)	C10—C11—C12—C13	179.52 (18)
C5—C4—C8—C9	171.77 (17)	C11—C12—C13—C14	0.5 (2)
C3—C4—C8—C9	−7.0 (3)	C11—N1—C14—C13	1.0 (2)
C4—C8—C9—C10	179.85 (16)	C12—C13—C14—N1	−0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.07	2.8525 (19)	151

Symmetry code: (i) −x+1, −y+1, −z+1.